Sulfuric Acid → Methyl 5-Iodosalicylate

HRID 368296

Reaction equation

HRID 368296 reaction equation
[I:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.[CH:12](OC)(OC)OC.S(=O)(=O)(O)O>CO>[CH3:12][O:8][C:7](=[O:9])[C:6]1[C:5](=[CH:4][CH:3]=[C:2]([I:1])[CH:10]=1)[OH:11]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 83885-Iodosalicylic acidHCID 9005Trimethyl orthoformate

Product 1

HCID 248910Methyl 5-Iodosalicylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Iodosalicylic acid (Aldrich Chemical Company, Milwaukee, Wis.) is converted to the methyl ester by reaction with methanol, trimethyl orthoformate and sulfuric acid. The 5-iodosalicylic acid methyl ester thus obtained is reacted with (trimethylsilyl)acetylene (Aldrich Chemical Company, Milwaukee, Wis.) in the presence of palladium. The trimethylsilyl group is removed and two equivalents of the resultant 5-acetylenylsalicylic acid methyl ester is reacted with 4,4'-dibromobiphenyl (Aldrich Chemical Company, Milwaukee, Wis.) in the presence of palladium as above. The resultant alkynyl analogue of Chrysamine G, 4,4'-bis(3-methoxycarbonyl-4-hydroxyphenylacetylenyl)-biphenyl is prepared by hydrolysis of the ester as described above.

Sources & evidence

ORD record
ord-41e292c8f77545939f90e40c8d409a74
Source dataset
uspto-grants-2000_10
Patent number
US06133259

Linked notes

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